I am a TripIt Pro subscriber, but it sure is handy to have Cortana keep track and monitor my flights too. I don't know exactly where she gets the flight data from, but all I see is a prompt to ask me if she wants to monitor my flights so I assume my email is being monitored.

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I enjoy playing and watching sports and love when my phone lets me know about upcoming games and the scores of those games. This is especially helpful for English Premier League football since I am so far removed from the timezone of when the games are being played. Cortana gives me the schedule and stats for my favorite team, including when I can watch it in local time.

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I am terrible at knowing the names and artists of songs so I enjoy using Cortana to identify music on the radio. The great thing is that you can then tap on the identified song and go into Xbox Music to hear more from the artist. All of your music searches are also found in your Cortana notebook for later viewing.

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• Could and should Microsoft bring Cortana to iOS, Android?  
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I enjoy good jokes, but am terrible at ever remembering those I hear. Simply say to Cortana 'tell me a joke' and she will say them out loud to you. My family enjoys hearing these at the dinner table and the jokes are usually pretty witty and clean.

You can also ask Cortana to sing to you and she does so in a very human voice.

Related

• Could and should Microsoft bring Cortana to iOS, Android?
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Other platforms support location-based reminders, but for some reason I have had the most success with Cortana. I am regularly given honey-do lists from my wife that include picking up supplies from the local hardware store and I usually forget something or can't remember to write it down in the first place.

I was blown away when I entered the Lowe's parking lot and a list popped up on my phone with everything I needed to pick up.

Related

• Could and should Microsoft bring Cortana to iOS, Android?
• The Windows phone: Why a longtime Android and Apple user converted
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Do you ever tell yourself that you have to discuss something with someone the next time you talk with them on the phone? With Cortana you can set a person-specific reminder so that when you call that person in the future a reminder pops up with the subject of what you wanted to talk with them about.

Related

• Could and should Microsoft bring Cortana to iOS, Android?
• The Windows phone: Why a longtime Android and Apple user converted
• Cortana integration with Windows 'Threshold' said to be looking more likely
• Six ways Windows Phone is better than iPhone